Synergistic Fungicidal Mixtures and Compositions Comprising 5-Fluoro-4-Imino-3-Methyl-1-Tosyl-3,4-Dihydropyrimidin-2(1H)-One for Fungal Control (SDHI)

ABSTRACT

5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one, and at least one fungicide to provide synergistic control of selected fungi, wherein the at least one fungicide is a succinate dehydrogenase-inhibitor.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of U.S. Provisional PatentApplication Ser. Nos. 61/922,616, 61/922,630, and 61/922,640, all filedDec. 31, 2013, which are expressly incorporated by reference herein.

FIELD OF THE INVENTION

This disclosure concerns a synergistic fungicidal composition containing(a) a compound of Formula I and (b) at least one fungicide selected fromthe group consisting of a strobilurin, for example pyraclostrobin,fluoxastrobin, azoxystrobin, trifloxystrobin, picoxystrobin, andkresoxim-methyl; a succinate dehydrogenase-inhibitor (SDHI), for examplefluxapyroxad, benzovindiflupyr, penthiopyrad, isopyrazam, bixafen,boscalid, penflufen, and fluopyram; an ergosterol biosynthesis-inhibitor(SBI), for example prothioconazole, epoxiconazole, cyproconazole,myclobutanil, prochloraz, metconazole, difenoconazole, tebuconazole,tetraconazole, fenbuconazole, propiconazole, fluquinconazole,flusilazole, flutriafol, and fenpropimorph; and a multi-site-inhibitor,for example mancozeb and chlorothalonil, or other commercial fungicidesto provide control of any plant fungal pathogen.

BACKGROUND AND SUMMARY

Fungicides are compounds, of natural or synthetic origin, which act toprotect plants against damage caused by fungi. Current methods ofagriculture rely heavily on the use of fungicides. In fact, some cropscannot be grown usefully without the use of fungicides. Using fungicidesallows a grower to increase the yield and the quality of the crop, andconsequently, increase the value of the crop. In most situations, theincrease in value of the crop is worth at least three times the cost ofthe use of the fungicide.

However, no one fungicide is useful in all situations and repeated usageof a single fungicide frequently leads to the development of resistanceto that and related fungicides. Consequently, research is beingconducted to produce fungicides and combinations of fungicides that aresafer, that have better performance, that require lower dosages, thatare easier to use, and that cost less.

Synergism occurs when the activity of two or more compounds exceeds theactivities of the compounds when used alone.

It is an object of this disclosure to provide synergistic compositionscomprising fungicidal compounds. It is a further object of thisdisclosure to provide processes that use these synergistic compositions.The synergistic compositions are capable of preventing or curing, orboth, diseases caused by fungi of the classes Ascomycetes andBasidiomycetes. In addition, the synergistic compositions have improvedefficacy against the Ascomycete and Basidiomycete pathogens, includingleaf blotch and brown rust of wheat. In accordance with this disclosure,synergistic compositions are provided along with methods for their use.

According to an exemplary embodiment of the present disclosure, asynergistic fungicidal mixture is provided including a fungicidallyeffective amount of the compound of Formula I, and at least onefungicidal succinate dehydrogenase inhibitor (SDHI).

According to another exemplary embodiment of the present disclosure, asynergistic fungicidal mixture is provided including a fungicidallyeffective amount of the compound of Formula I, and at least oneadditional fungicide in which the at least one additional fungicide is asuccinate dehydrogenase inhibitor (SDHI).

According to yet another exemplary embodiment of the present disclosure,a synergistic, fungicidal composition is provided including afungicidally effective amount of the mixtures and an agriculturallyacceptable adjuvant or carrier.

In certain embodiments, the SDHI and/or the at least one additionalfungicide is selected from the group consisting of fluxapyroxad,benzovindiflupyr, penthiopyrad, isopyrazam, boscalid, and fluopyram.

In certain embodiments, the SDHI and/or the at least one additionalfungicide is fluxapyroxad.

In certain embodiments, the SDHI and/or the at least one additionalfungicide is penthiopyrad.

In certain embodiments, the SDHI and/or the at least one additionalfungicide is benzovindiflupyr.

In certain embodiments, the SDHI and/or the at least one additionalfungicide is fluopyram.

In certain embodiments, the SDHI and/or the at least one additionalfungicide is isopyrazam.

In certain embodiments, the SDHI and/or the at least one additionalfungicide is boscalid.

In certain embodiments, the concentration ratio of the Compound ofFormula I to fluxapyroxad is between about 4.4:1 and about 6.3:1.

In certain embodiments, the concentration ratio of the Compound ofFormula I to benzovindiflupyr is between about 1:3 and about 7.9:1.

In certain embodiments, the concentration ratio of the Compound ofFormula I to penthiopyrad is between about 1:4.3 and about 1:1.9.

In certain embodiments, the concentration ratio of the Compound ofFormula I to isopyrazam is between about 1:1.3 and about 1:1.

In certain embodiments, the concentration ratio of the Compound ofFormula I to boscalid is between about 1:13.2 and about 1:1.3.

In certain embodiments, the concentration ratio of the Compound ofFormula I to fluopyram is between about 1:27.6 and about 1:3.6.

In certain embodiments, the mixture provides control of a fungalpathogen and the fungal pathogen is one of Leaf Blotch of Wheat(Mycosphaerella graminicola; anamorph: Septoria tritici), Wheat BrownRust (Puccinia triticina), Stripe Rust (Puccinia striiformis f. sp.tritici), Scab of Apple (Venturia inaequalis), Blister Smut of Maize(Ustilago maydis), Powdery Mildew of Grapevine (Uncinula necator),Barley scald (Rhynchosporium secalis), Blast of Rice (Magnaporthegrisea), Rust of Soybean (Phakopsora pachyrhizi), Glume Blotch of Wheat(Leptosphaeria nodorum), Powdery Mildew of Wheat (Blumeria graminis f.sp. tritici), Powdery Mildew of Barley (Blumeria graminis f. sp.hordei), Powdery Mildew of Cucurbits (Erysiphe cichoracearum),Anthracnose of Cucurbits (Glomerella lagenarium), Leaf Spot of Beet(Cercospora beticola), Early Blight of Tomato (Alternaria solani), andNet Blotch of Barley (Pyrenophora teres).

In certain embodiments, the mixture provides control of a fungalpathogen and the fungal pathogen is Leaf Blotch of Wheat (Mycosphaerellagraminicola; anamorph: Septoria tritici).

DETAILED DESCRIPTION

The present disclosure concerns a synergistic fungicidal mixturecomprising a fungicidally effective amount of (a) a compound of FormulaI and (b) at least one fungicide selected from the group consisting of astrobilurin, for example pyraclostrobin, fluoxastrobin, azoxystrobin,trifloxystrobin, picoxystrobin, and kresoxim-methyl, a succinatedehydrogenase-inhibitor, for example fluxapyroxad, benzovindiflupyr,penthiopyrad, isopyrazam, bixafen, boscalid, penflufen, and fluopyram,an ergosterol biosynthesis-inhibitor, for example prothioconazole,epoxiconazole, cyproconazole, myclobutanil, prochloraz, metconazole,difenoconazole, tebuconazole, tetraconazole, fenbuconazole,propiconazole, fluquinconazole, flusilazole, flutriafol, fenpropimorph,and prochloaz, and a multi-site-inhibitor, for example mancozeb andchlorothalonil, or other commercial fungicides to provide control of anyplant fungal pathogen.

As used herein, the compound of Formula I is5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one. Thecompound of Formula I provides control of a variety of pathogens ineconomically important crops including, but not limited to, the causalagent of leaf blotch in wheat, Septoria tritici (SEPTTR).

As used herein, epoxiconazole is the common name for(2RS,3SR)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,2,4-triazoleand possesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Epoxiconazole provides broad spectrum control, withpreventive and curative action, of diseases caused by Ascomycetes,Basidiomycetes and Deuteromycetes in bananas, cereals, coffee, rice andsugar beet.

As used herein, cyproconazole is the common name for(2RS,3RS;2RS,3SR)-2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-oland possesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Cyproconazole provides control of Septoria, rust, powderymildew, Rhynchosporium, Cercospora and Ramularia in cereals and sugarbeet; and rust, Mycena, Sclerotinia and Rhizoctonia in coffee and turf.

As used herein, metconazole is the common name for(1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanoland possesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Metconazole provides control of a wide range of foliardiseases on cereals and other crops, and is particularly effectiveagainst Fusarium, Septoria and rust diseases on cereals.

As used herein, myclobutanil is the common name forα-butyl-α-(4-chlorophenyl)-1H-1,2,4-triazole-1-propanenitrile andpossesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Myclobutanil provides control of Ascomycetes, FungiImperfecti and Basidiomycetes on a wide variety of crops.

As used herein, propiconazole is the common name for(±)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazoleand possesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Propiconazole provides control of a broad range ofdiseases on a variety of crops. For example, on cereals it controlsdiseases caused by Cochliobolus sativus, Erysiphe graminis,Leptosphaeria nodorum, Puccinia spp., Pyrenophora teres, Pyrenophoratritici-repentis, Rhynchosporium secalis and Septoria spp, and inbananas it controls diseases caused by Mycosphaerella musicola andMycosphaerella fijiensis var. difformis. Other uses are in turf, againstSclerotinia homoeocarpa, Rhizoctonia solani, Puccinia spp, and Erysiphegraminis; in rice, against Rhizoctonia solani, Helminthosporium oryzaeand dirty panicle complex; in coffee, against Hemileia vastatrix; inpeanuts, against Cercospora spp.; in stone fruit, against Moniliniaspp., Podosphaera spp., Sphaerotheca spp. and Tranzschelia spp.; and inmaize, against Helminthosporium spp.

As used herein, prothioconazole is the common name2-[(2RS)-2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2H-1,2,4-triazole-3(4H)-thione and possesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Prothioconazole provides control of diseases such aseyespot (Pseudocercosporella herpotrichoides), Fusarium ear blight(Fusarium spp., Microdochium nivale), leaf blotch diseases (Septoriatritici, Leptosphaeria nodorum, Pyrenophora spp., Rhynchosporiumsecalis, etc.), rust (Puccinia spp.) and powdery mildew (Blumeriagraminis), by foliar application, in wheat, barley and other crops.

As used herein, picoxystrobin is the common name for methyl(E)-3-methoxy-2-[2-(6-trifluoromethyl-2-pyridyloxymethyl)phenyl]acrylateand possesses the following structure:

Its fungicidal activity is described in The e-Pesticide Manual, Version5.2, 2011. Exemplary uses of picoxystrobin include, but are not limitedto, broad-spectrum disease control in cereals, including Mycosphaerellagraminicola, Phaeosphaeria nodorum, Puccinia recondita (brown rust),Helminthosporium tritici-repentis (tan spot) and Blumeria graminis f.sp. tritici (strobilurin-sensitive powdery mildew) in wheat;Helminthosporium teres (net blotch), Rhynchosporium secalis, Pucciniahordei (brown rust) and Erysiphe graminis f. sp. hordei(strobilurin-sensitive powdery mildew) in barley; Puccinia coronata andHelminthosporium avenae in oats; and Puccinia recondita andRhynchosporium secalis in rye.

As used herein, trifloxystrobin is the common name for methyl(αE)-α-(methoxyimino)-2-[[[[(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]-benzeneacetateand possesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Trifloxystrobin provides broad-spectrum control of avariety of fungal pathogens on a wide variety of fruits, vegetables, andcrops.

As used herein, azoxystrobin is the common name for methyl(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylateand possesses the following structure:

Its fungicidal activity is exemplified in The e-Pesticide Manual,Version 5.2, 2011. Exemplary uses of azoxystrobin include, but are notlimited to, control of the following pathogens: Erysiphe graminis,Puccinia spp., Leptosphaeria nodorum, Septoria tritici and Pyrenophorateres on temperate cereals; Pyricularia oryzae and Rhizoctonia solani onrice; Plasmopara viticola and Uncinula necator on vines; Sphaerothecafuliginea and Pseudoperonospora cubensis on cucurbitaceae; Phytophthorainfestans and Alternaria solani on potato and tomato; Mycosphaerellaarachidis, Rhizoctonia solani and Sclerotium rolfsii on peanut;Monilinia spp. and Cladosporium carpophilum on peach; Pythium spp. andRhizoctonia solani on turf; Mycosphaerella spp. on banana; Cladosporiumcaryigenum on pecan; Elsinoë fawcettii, Colletotrichum spp. andGuignardia citricarpa on citrus; Colletotrichum spp. and Hemileiavastatrix on coffee.

As used herein, fluoxastrobin is the common name for(E)-{2-[6-(2-chlorophenoxy)-5-fluoropyrimidin-4-yloxy]phenyl}(5,6-dihydro-1,4,2-dioxazin-3-yl)methanoneO-methyloxime and possesses the following structure:

Its fungicidal activity is exemplified in The e-Pesticide Manual,Version 5.2, 2011. Exemplary uses of fluoxastrobin include, but are notlimited to, use as a foliar spray in cereals for control of Septorialeaf spot diseases (Septoria tritici and Leptosphaeria nodorum), rustsof wheat and barley (Puccinia recondita, P. striiformis, P. hordei),Helminthosporium diseases like Pyrenophora teres (net blotch of barley)and Pyrenophora tritici-repentis (tan spot).

As used herein, boscalid is the common name for2-chloro-N-(4′-chloro[1,1′-biphenyl]-2-yl)-3-pyridinecarboxamide andpossesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Boscalid provides control of powdery mildew, Alternariaspp., Botrytis spp., Sclerotinia spp., Mycosphaerella spp. and Moniliaspp. on grapes, turf, and a range of fruit, vegetables and ornamentals.

As used herein, isopyrazam is the common name for a mixture of the 2 synand 2 anti isomers of3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9RS)-1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl]pyrazole-4-carboxamideand3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9SR)-1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl]pyrazole-4-carboxamide,respectively, and possesses the following structures:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Isopyrazam provides control of Septoria tritici and rustsin wheat, and Ramularia in barley.

As used herein, fluxapyroxad is the common name for3-(difluoromethyl)-1-methyl-N-(3′,4′,5′-trifluorobiphenyl-2-yl)pyrazole-4-carboxamideand possesses the following structure:

Its fungicidal activity is exemplified in Agrow Intelligence(https://www.agra-net.net/agra/agrow/databases/agrow-intelligence/).Exemplary uses of fluxapyroxad include, but are not limited to, thecontrol of plant pathogens, such as Helminthosporium teres (net blotch),Rhynchosporium secalis (leaf scald), Puccinia hordei (brown rust), andErysiphe graminis f. sp. hordei (powdery mildew) in a range of crops,such as barley, maize, and soybeans.

As used herein, penthiopyrad is the common name forN-[2-(1,3-dimethylbutyl)-3-thienyl]-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamideand possesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Penthiopyrad provides control of rust and Rhizoctoniadiseases, as well as grey mold, powdery mildew and apple scab.

As used herein, benzovindiflupyr is the common name forN-[(1RS,4SR)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamideand possesses the following structure:

Its fungicidal activity is exemplified in Agrow Intelligence(https://www.agra-net.net/agra/agrow/databases/agrow-intelligence/).Exemplary uses of benzovindiflupyr include, but are not limited to,controlling a variety of pathogens such as Botrytis spp., Erysiphe spp.,Rhizoctonia spp., Septoria spp., Phytophthora spp., Pythium spp.,Phakopsora pachyrhizi, and Puccinia recondita, in a range of cropsincluding vines, cereals, soybeans, cotton, and fruit and vegetablecrops.

As used herein, fluquinconazole is the common name for3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-oneand possesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Fluquinconazole provides control of a wide range ofAscomycetes, Deuteromycetes and Basidiomycetes. For example, foliarapplication provides control of Leptosphaeria nodorum, Septoria tritici,Puccinia spp., Ustilago nuda, Tilletia caries, Tilletia controversa,Urocystis occulta, Pyrenophora teres, and Pyrenophora graminea incereals; Cercospora spp., Microsphaera diffusa, and Phakopsorapachyrhizi in soybeans; Venturia spp., and Podosphaera leucotricha inpome fruit; and Uncinula necator in vines.

As used herein, difenoconazole is the common name for1-[[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazoleand possesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Difenoconazole provides broad-spectrum fungicidalcontrol, with preventative and curative action, of diseases caused byAscomycetes, Basidiomycetes and Deuteromycetes.

As used herein, pyraclostrobin is the common name for methylN-[2-[[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy]methyl]phenyl]-N-methoxycarbamateand possesses the following structure:

Its fungicidal activity is exemplified in The e-Pesticide Manual,Version 5.2, 2011. Exemplary uses of pyraclostrobin include, but are notlimited to, the control of major plant pathogens, such as Septoriatritici, Puccinia spp., Drechslera tritici-repentis and Pyrenophorateres in cereals.

As used herein, fluopyram is the common name forN-[2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl]-2-(trifluoromethyl)benzamideand possesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Fluopyram provides control of grey mold, powdery mildewand sclerotinia and monilinia diseases in a variety of fruits,vegetables and field crops.

As used herein, flutriafol is the common name for(RS)-2,4′-difluoro-α-(1H-1,2,4-triazol-1-ylmethyl)benzhydryl alcohol andpossesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Flutriafol provides control of a broad spectrum of leafand ear diseases, including but not limited to, Erysiphe graminis,Rhynchosporium secalis, Septoria spp., Puccinia spp., Helminthosporiumteres and Helminthosporium tritici-repentis in cereals.

As used herein, kresoxim-methyl is the common name for methyl(E)-methoxyimino[2-(o-tolyloxymethyl)phenyl]acetate and possesses thefollowing structure:

Its fungicidal activity is exemplified in The e-Pesticide Manual,Version 5.2, 2011. Exemplary uses of kresoxim-methyl include, but arenot limited to, the control of scab in apples and pears (Venturia spp.);powdery mildew on apples (Podosphaera leucotricha), vines (Uncinulanecator), cucurbits (Sphaerotheca fuliginea) and sugar beet (Erysiphebetae); mildew (Erysiphe graminis), scald (Rhynchosporium secalis), netblotch (Pyrenophora teres) and glume blotch (Septoria nodorum) oncereals; and mildew (Leveillula taurica, Erysiphe spp., Alternaria spp.)on vegetables.

As used herein, chlorothalonil is the common nametetrachloroisophthalonitrile and possesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Chlorothalonil provides control of many fungal diseasesin a wide range of crops, including pome fruit, stone fruit, almonds,citrus fruit, bush and cane fruit, cranberries, strawberries, pawpaws,bananas, mangoes, coconut palms, oil palms, rubber, pepper, vines, hops,vegetables, cucurbits, tobacco, coffee, tea, rice, soybeans, peanuts,potatoes, sugar beet, cotton, maize, ornamentals, mushrooms, and turf.

As used herein, mancozeb is the common name for[[2-[(dithiocarboxy)amino]ethyl]carbamodithioato(2-)-κS,κS′]manganesemixture with[[2-[(dithiocarboxy)amino]ethyl]carbamodithioato(2-)-κS,κS′]zinc andpossesses the following structure:

Its fungicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009. Mancozeb provides control of a wide range of fungalpathogens on a variety of fruits, vegetables and field crops.

In the compositions described herein, the concentration ratio of thecompound of Formula I at which the fungicidal effect is synergistic withthe other fungicides against SEPTTR in protectant and curativeapplications lies within the range of about 1:250 and about 787:1. Inone embodiment, the concentration ratio of the compound of Formula I atwhich the fungicidal effect is synergistic with the other fungicides inprotectant applications lies within the range of about 1:272 and about787:1. In another embodiment, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic with the otherfungicides in curative applications lies within the range of about 1:250and about 120:1.

In the compositions described herein, the concentration ratio of thecompound of Formula I at which the fungicidal effect is synergistic withthe SBIs against SEPTTR in protectant and curative applications lieswithin the range of about 1:27 and about 787:1. In one embodiment, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with the SBIs against SEPTTR in protectantapplications lies within the range of about 1:4 and about 787:1. Inanother embodiment, the concentration ratio of the compound of Formula Iat which the fungicidal effect is synergistic with the SBIs againstSEPTTR in curative applications lies within the range of about 1:27 andabout 120:1. In some embodiments, the concentration ratio of thecompound of Formula I at which the fungicidal effect is synergistic withepoxiconazole against SEPTTR in protectant and curative applicationslies within the range of about 3.6:1 and about 20:1. In one embodiment,the concentration ratio of the compound of Formula I at which thefungicidal effect is synergistic with epoxiconazole against SEPTTR inprotectant applications is about 20:1, and in another embodiment, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with epoxiconazole against SEPTTR in curativeapplications is about 3.6:1. In some embodiments, the concentrationratio of the compound of Formula I at which the fungicidal effect issynergistic with cyproconazole against SEPTTR in protectant and curativeapplications lies within the range of about 1:3 and about 4.5:1. In oneembodiment, the concentration ratio of the compound of Formula I atwhich the fungicidal effect is synergistic with cyproconazole againstSEPTTR in protectant applications is about 4.5:1, and in anotherembodiment, the concentration ratio of the compound of Formula I atwhich the fungicidal effect is synergistic with cyproconazole againstSEPTTR in curative applications is about 1:3. In some embodiments, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with metconazole against SEPTTR in protectant andcurative applications lies within the range of about 2.2:1 and about30:1. In one embodiment, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic with metconazoleagainst SEPTTR in protectant applications is about 30:1, and in anotherembodiment, the concentration ratio of the compound of Formula I atwhich the fungicidal effect is synergistic with metconazole againstSEPTTR in curative applications is about 2.2:1. In some embodiments, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with myclobutanil against SEPTTR in protectant andcurative applications lies within the range of about 1:27 and about 1:4.In one embodiment, the concentration ratio of the compound of Formula Iat which the fungicidal effect is synergistic with the myclobutanilagainst SEPTTR in protectant applications is about 1:4, and in anotherembodiment, the concentration ratio of the compound of Formula I atwhich the fungicidal effect is synergistic with myclobutanil againstSEPTTR in curative applications is about 1:27. In some embodiments, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with propiconazole against SEPTTR in protectantand curative applications lies within the range of about 1:2.1 and about30:1. In one embodiment, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic withpropiconazole against SEPTTR in protectant applications is about 30:1,and in another embodiment, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic withpropiconazole against SEPTTR in curative applications is about 1:2.1. Insome embodiments, the concentration ratio of the compound of Formula Iat which the fungicidal effect is synergistic with prothioconazoleagainst SEPTTR in protectant and curative applications lies within therange of about 1:21.6 and about 2:1. In one embodiment, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with prothioconazole against SEPTTR in protectantapplications is about 2:1, and in another embodiment, the concentrationratio of the compound of Formula I at which the fungicidal effect issynergistic with prothioconazole against SEPTTR in curative applicationsis about 1:21.6. In some embodiments, the concentration ratio of thecompound of Formula I at which the fungicidal effect is synergistic withfluquinconazole against SEPTTR in protectant and curative applicationslies within the range of about 1:1.3 and about 170:1. In one embodiment,the concentration ratio of the compound of Formula I at which thefungicidal effect is synergistic with the fluquinconazole against SEPTTRin protectant applications is about 170:1, and in another embodiment,the concentration ratio of the compound of Formula I at which thefungicidal effect is synergistic with fluquinconazole against SEPTTR incurative applications is about 1:1.3. In some embodiments, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with difenoconazole against SEPTTR in protectantand curative applications lies within the range of about 120:1 and about787:1. In one embodiment, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic withdifenoconazole against SEPTTR in protectant applications is about 787:1,and in another embodiment, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic withdifenoconazole against SEPTTR in curative applications is about 120:1.In some embodiments, the concentration ratio of the compound of FormulaI at which the fungicidal effect is synergistic with flutriafol againstSEPTTR in protectant and curative applications lies within the range ofabout 1:20.6 and about 5.1:1. In one embodiment, the concentration ratioof the compound of Formula I at which the fungicidal effect issynergistic with flutriafol against SEPTTR in protectant applications isabout 5.1:1, and in another embodiment, the concentration ratio of thecompound of Formula I at which the fungicidal effect is synergistic withflutriafol against SEPTTR in curative applications is about 1:20.6.

In the compositions described herein, the concentration ratio of thecompound of Formula I at which the fungicidal effect is synergistic withthe strobilurins against SEPTTR in protectant and curative applicationslies within the range of about 1:250 and about 42:1. In one embodiment,the concentration ratio of the compound of Formula I at which thefungicidal effect is synergistic with the strobilurins against SEPTTR inprotectant applications lies within the range of about 1:21.2 and about42:1. In another embodiment, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic with thestrobilurins against SEPTTR in curative applications lies within therange of about 1:250 and about 20:1. In some embodiments, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with picoxystrobin against SEPTTR in protectantand curative applications lies within the range of about 1:30 and about1:2.6. In one embodiment, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic withpicoxystrobin against SEPTTR in protectant applications is about 1:2.6,and in another embodiment, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic withpicoxystrobin against SEPTTR in curative applications lies is about1:30. In some embodiments, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic withtrifloxystrobin against SEPTTR in protectant and curative applicationslies within the range of about 1:9.7 and about 4:1. In one embodiment,the concentration ratio of the compound of Formula I at which thefungicidal effect is synergistic with trifloxystrobin against SEPTTR inprotectant applications is about 4:1, and in another embodiment, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with trifloxystrobin against SEPTTR in curativeapplications is about 1:9.7. In some embodiments, the concentrationratio of the compound of Formula I at which the fungicidal effect issynergistic with azoxystrobin against SEPTTR in protectant and curativeapplications lies within the range of about 1:4.6 and about 2:1. In oneembodiment, the concentration ratio of the compound of Formula I atwhich the fungicidal effect is synergistic with azoxystrobin againstSEPTTR in protectant applications is about 2:1, and in anotherembodiment, the concentration ratio of the compound of Formula I atwhich the fungicidal effect is synergistic with azoxystrobin againstSEPTTR in curative applications is about 1:4.6. In some embodiments, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with fluoxastrobin against SEPTTR in protectantand curative applications lies within the range of about 1:1.6 and about7:1. In one embodiment, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic withfluoxastrobin against SEPTTR in protectant applications is about 7:1,and in another embodiment, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic withfluoxastrobin against SEPTTR in curative applications is about 1:1.6. Insome embodiments, the concentration ratio of the compound of Formula Iat which the fungicidal effect is synergistic with pyraclostrobinagainst SEPTTR in protectant and curative applications lies within therange of about 20:1 and about 42:1. In one embodiment, the concentrationratio of the compound of Formula I at which the fungicidal effect issynergistic with pyraclostrobin against SEPTTR in protectantapplications is about 42:1, and in another embodiment, the concentrationratio of the compound of Formula I at which the fungicidal effect issynergistic with pyraclostrobin against SEPTTR in curative applicationsis about 20:1. In some embodiments, the concentration ratio of thecompound of Formula I at which the fungicidal effect is synergistic withkresoxim-methyl against SEPTTR in protectant and curative applicationslies within the range of about 1:250 and about 1:21.2. In oneembodiment, the concentration ratio of the compound of Formula I atwhich the fungicidal effect is synergistic with the kresoxim-methylagainst SEPTTR in protectant applications is about 1:21.2, and inanother embodiment, the concentration ratio of the compound of Formula Iat which the fungicidal effect is synergistic with kresoxim-methylagainst SEPTTR in curative applications is about 1:250.

In the compositions described herein, the concentration ratio of thecompound of Formula I at which the fungicidal effect is synergistic withthe SDHIs against SEPTTR in protectant and curative applications lieswithin the range of about 1:28 and about 8:1. In one embodiment, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with the SDHIs against SEPTTR in protectantapplications lies within the range of about 1:3.6 and about 8:1. Inanother embodiment, the concentration ratio of the compound of Formula Iat which the fungicidal effect is synergistic with the SDHIs againstSEPTTR in curative applications lies within the range of about 1:28 andabout 6.3:1. In some embodiments, the concentration ratio of thecompound of Formula I at which the fungicidal effect is synergistic withboscalid against SEPTTR in protectant and curative applications lieswithin the range of about 1:13.2 and about 1:1.3. In one embodiment, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with boscalid against SEPTTR in protectantapplications is about 1:1.3, and in another embodiment, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with boscalid against SEPTTR in curativeapplications is about 1:13.2. In some embodiments, the concentrationratio of the compound of Formula I at which the fungicidal effect issynergistic with isopyrazam against SEPTTR in protectant and curativeapplications lies within the range of about 1:1.3 and about 1:1. In oneembodiment, the concentration ratio of the compound of Formula I atwhich the fungicidal effect is synergistic with isopyrazam againstSEPTTR in protectant applications is about 1:1.3, and in anotherembodiment, the concentration ratio of the compound of Formula I atwhich the fungicidal effect is synergistic with isopyrazam againstSEPTTR in curative applications is about 1:1. In some embodiments, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with fluxapyroxad against SEPTTR in protectant andcurative applications lies within the range of about 4.4:1 and about6.3:1. In one embodiment, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic withfluxapyroxad against SEPTTR in protectant applications is about 4.4:1,and in another embodiment, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic withfluxapyroxad against SEPTTR in curative applications is about 6.3:1. Insome embodiments, the concentration ratio of the compound of Formula Iat which the fungicidal effect is synergistic with penthiopyrad againstSEPTTR in protectant and curative applications lies within the range ofabout 1:4.3 and about 1:1.9. In one embodiment, the concentration ratioof the compound of Formula I at which the fungicidal effect issynergistic with penthiopyrad against SEPTTR in protectant applicationsis about 1:1.9, and in another embodiment, the concentration ratio ofthe compound of Formula I at which the fungicidal effect is synergisticwith penthiopyrad against SEPTTR in curative applications is about1:4.3. In some embodiments, the concentration ratio of the compound ofFormula I at which the fungicidal effect is synergistic withbenzovindiflupyr against SEPTTR in protectant and curative applicationslies within the range of about 1:3 and about 7.9:1. In one embodiment,the concentration ratio of the compound of Formula I at which thefungicidal effect is synergistic with benzovindiflupyr against SEPTTR inprotectant applications is about 7.9:1, and in another embodiment, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with benzovindiflupyr against SEPTTR in curativeapplications is about 1:3. In some embodiments, the concentration ratioof the compound of Formula I at which the fungicidal effect issynergistic with fluopyram against SEPTTR in protectant and curativeapplications lies within the range of about 1:27.6 and about 1:3.6. Inone embodiment, the concentration ratio of the compound of Formula I atwhich the fungicidal effect is synergistic with fluopyram against SEPTTRin protectant applications is about 1:3.6, and in another embodiment,the concentration ratio of the compound of Formula I at which thefungicidal effect is synergistic with fluopyram against SEPTTR incurative applications is about 1:27.6.

In the compositions described herein, the concentration ratio of thecompound of Formula I at which the fungicidal effect is synergistic withthe multi-site inhibitors against SEPTTR in protectant applications lieswithin the range of about 1:272 and about 1:219. In some embodiments,the concentration ratio of the compound of Formula I at which thefungicidal effect is synergistic with chlorothalonil against SEPTTR inprotectant applications is about 1:219. In some embodiments, theconcentration ratio of the compound of Formula I at which the fungicidaleffect is synergistic with mancozeb against SEPTTR in protectantapplications is about 1:272.

The rate at which the synergistic composition is applied will dependupon the particular type of fungus to be controlled, the degree ofcontrol required and the timing and method of application. In general,the compositions described herein can be applied at an application rateof between about 40 grams per hectare (g/ha) and about 2600 g/ha basedon the total amount of active ingredients in the composition.

The compositions comprising the compound of Formula I and an SBI can beapplied at an application rate of between about 40 g/ha and about 600g/ha based on the total amount of active ingredients in the composition.Epoxiconazole is applied at a rate of between about 50 g/ha and about250 g/ha, and the compound of Formula I is applied at a rate betweenabout 15 g/ha and about 100 g/ha. Cyproconazole is applied at a rate ofbetween about 50 g/ha and about 250 g/ha, and the compound of Formula Iis applied at a rate between about 15 g/ha and about 100 g/ha.Metconazole is applied at a rate of between about 50 g/ha and about 250g/ha, and the compound of Formula I is applied at a rate between about15 g/ha and about 100 g/ha. Myclobutanil is applied at a rate of betweenabout 30 g/ha and about 150 g/ha, and the compound of Formula I isapplied at a rate between about 15 g/ha and about 100 g/ha.Propiconazole is applied at a rate of between about 50 g/ha and about250 g/ha, and the compound of Formula I is applied at a rate betweenabout 15 g/ha and about 100 g/ha. Prothioconazole is applied at a rateof between about 50 g/ha and about 250 g/ha, and the compound of FormulaI is applied at a rate between about 15 g/ha and about 100 g/ha.Fluquinconazole is applied at a rate of between about 25 g/ha and about500 g/ha, and the compound of Formula I is applied at a rate betweenabout 15 g/ha and about 100 g/ha. Difenoconazole is applied at a rate ofbetween about 30 g/ha and about 125 g/ha, and the compound of Formula Iis applied at a rate between about 15 g/ha and about 100 g/ha.Flutriafol is applied at a rate of between about 60 g/ha and about 200g/ha, and the compound of Formula I is applied at a rate between about15 g/ha and about 100 g/ha.

The compositions comprising the compound of Formula I and a strobilurincan be applied at an application rate of between about 65 g/ha and about650 g/ha based on the total amount of active ingredients in thecomposition. Picoxystrobin is applied at a rate of between about 50 g/haand about 250 g/ha, and the compound of Formula I is applied at a ratebetween about 15 g/ha and about 100 g/ha. Trifloxystrobin is applied ata rate of between about 50 g/ha and about 550 g/ha, and the compound ofFormula I is applied at a rate between about 15 g/ha and about 100 g/ha.Azoxystrobin is applied at a rate of between about 100 g/ha and about375 g/ha, and the compound of Formula I is applied at a rate betweenabout 15 g/ha and about 100 g/ha. Fluoxastrobin is applied at a rate ofbetween about 75 g/ha and about 200 g/ha, and the compound of Formula Iis applied at a rate between about 15 g/ha and about 100 g/ha.Pyraclostrobin is applied at a rate of between about 50 g/ha and about250 g/ha, and the compound of Formula I is applied at a rate betweenabout 15 g/ha and about 100 g/ha. Kresoxim-methyl is applied at a rateof between about 50 g/ha and about 250 g/ha and the compound of FormulaI is applied at a rate between about 15 g/ha and about 100 g/ha.

The compositions comprising the compound of Formula I and an SDHI can beapplied at an application rate of between about 40 g/ha and about 725g/ha based on the total amount of active ingredients in the composition.Boscalid is applied at a rate of between about 100 g/ha and about 625g/ha, and the compound of Formula I is applied at a rate between about15 g/ha and about 100 g/ha. Isopyrazam is applied at a rate of betweenabout 25 g/ha and about 300 g/ha, and the compound of Formula I isapplied at a rate between about 15 g/ha and about 100 g/ha. Fluxapyroxadis applied at a rate of between about 45 g/ha and about 200 g/ha, andthe compound of Formula I is applied at a rate between about 15 g/ha andabout 100 g/ha. Penthiopyrad is applied at a rate of between about 100g/ha and about 400 g/ha, and the compound of Formula I is applied at arate between about 15 g/ha and about 100 g/ha. Benzovindiflupyr isapplied at a rate of between about 25 g/ha and about 300 g/ha, and thecompound of Formula I is applied at a rate between about 15 g/ha andabout 100 g/ha. Fluopyram is applied at a rate of between about 30 g/haand about 250 g/ha, and the compound of Formula I is applied at a ratebetween about 15 g/ha and about 100 g/ha.

The compositions comprising the compound of Formula I and a multi-siteinhibitor can be applied at an application rate of between about 1015g/ha and about 2600 g/ha based on the total amount of active ingredientsin the composition. Chlorothalonil is applied at a rate of between about1000 g/ha and about 2500 g/ha, and the compound of Formula I is appliedat a rate between about 15 g/ha and about 100 g/ha. Mancozeb is appliedat a rate of between about 1500 g/ha and about 2000 g/ha, and thecompound of Formula I is applied at a rate between about 15 g/ha andabout 100 g/ha.

The components of the synergistic mixture described herein can beapplied either separately or as part of a multipart fungicidal system.

The synergistic mixture of the present disclosure can be applied inconjunction with one or more other fungicides to control a wider varietyof undesirable diseases. When used in conjunction with otherfungicide(s), the presently claimed compounds may be formulated with theother fungicide(s), tank mixed with the other fungicide(s) or appliedsequentially with the other fungicide(s). Such other fungicides mayinclude 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol,8-hydroxyquinoline sulfate, ametoctradin, amisulbrom, antimycin,Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis,Bacillus subtilis strain QST713, benalaxyl, benomyl,benthiavalicarb-isopropyl, benzylaminobenzene-sulfonate (BABS) salt,bicarbonates, biphenyl, bismerthiazol, bitertanol, bixafen,blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole,bupirimate, calcium polysulfide, captafol, captan, carbendazim,carboxin, carpropamid, carvone, chlazafenone, chloroneb, chlorothalonil,chlozolinate, Coniothyrium minitans, copper hydroxide, copper octanoate,copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprousoxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil,dazomet, debacarb, diammonium ethylenebis-(dithiocarbamate),dichlofluanid, dichlorophen, diclocymet, diclomezine, dichloran,diethofencarb, difenoconazole, difenzoquat ion, diflumetorim,dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton,dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine,dodine free base, edifenphos, enestrobin, enestroburin, epoxiconazole,ethaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil,fenpropidin, fenpropimorph, fenpyrazamine, fentin, fentin acetate,fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph,fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole,flusilazole, flusulfamide, flutianil, flutolanil, flutriafol,fluxapyroxad, folpet, formaldehyde, fosetyl, fosetyl-aluminum,fuberidazole, furalaxyl, furametpyr, guazatine, guazatine acetates,GY-81, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imazalilsulfate, imibenconazole, iminoctadine, iminoctadine triacetate,iminoctadine tris(albesilate), iodocarb, ipconazole, ipfenpyrazolone,iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam,isotianil, kasugamycin, kasugamycin hydrochloride hydrate,kresoxium-methyl, laminarin, mancopper, mancozeb, mandipropamid, maneb,mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, mercuric chloride,mercuric oxide, mercurous chloride, metalaxyl, metalaxyl-M, metam,metam-ammonium, metam-potassium, metam-sodium, metconazole,methasulfocarb, methyl iodide, methyl isothiocyanate, metiram,metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam,nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oleic acid (fattyacids), orysastrobin, oxadixyl, oxine-copper, oxpoconazole fumarate,oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen,pentachlorophenol, pentachlorophenyl laurate, penthiopyrad,phenylmercury acetate, phosphonic acid, phthalide, picoxystrobin,polyoxin B, polyoxins, polyoxorim, potassium bicarbonate, potassiumhydroxyquinoline sulfate, probenazole, prochloraz, procymidone,propamocarb, propamocarb hydrochloride, propiconazole, propineb,proquinazid, prothioconazole, pyraclostrobin, pyrametostrobin,pyraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox,pyrimethanil, pyriofenone, pyroquilon, quinoclamine, quinoxyfen,quintozene, Reynoutria sachalinensis extract, sedaxane, silthiofam,simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodiumpentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, tar oils,tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole,thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl,tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole,tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole,validamycin, valifenalate, valiphenal, vinclozolin, zineb, ziram,zoxamide, Candida oleophila, Fusarium oxysporum, Gliocladium spp.,Phlebiopsis gigantea, Streptomyces griseoviridis, Trichoderma spp.,(RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide,1,2-dichloropropane, 1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate,1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitropropane,2-(2-heptadecyl-2-imidazolin-1-yl)ethanol,2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide,2-methoxyethylmercury acetate, 2-methoxyethylmercury chloride,2-methoxyethylmercury silicate, 3-(4-chlorophenyl)-5-methylrhodanine,4-(2-nitroprop-1-enyl)phenyl thiocyanateme, ampropylfos, anilazine,azithiram, barium polysulfide, Bayer 32394, benodanil, benquinox,bentaluron, benzamacril, benzamacril-isobutyl, benzamorf, binapacryl,bis(methylmercury) sulfate, bis(tributyltin) oxide, buthiobate, cadmiumcalcium copper zinc chromate sulfate, carbamorph, CECA, chlobenthiazone,chloraniformethan, chlorfenazole, chlorquinox, climbazole, copperbis(3-phenylsalicylate), copper zinc chromate, cufraneb, cuprichydrazinium sulfate, cuprobam, cyclafuramid, cypendazole, cyprofuram,decafentin, dichlone, dichlozoline, diclobutrazol, dimethirimol,dinocton, dinosulfon, dinoterbon, dipyrithione, ditalimfos, dodicin,drazoxolon, EBP, ESBP, etaconazole, etem, ethirim, fenaminosulf,fenapanil, fenitropan, fluotrimazole, furcarbanil, furconazole,furconazole-cis, furmecyclox, furophanate, glyodine, griseofulvin,halacrinate, Hercules 3944, hexylthiofos, ICIA0858, isopamphos,isovaledione, mebenil, mecarbinzid, metazoxolon, methfuroxam,methylmercury dicyandiamide, metsulfovax, milneb, mucochloric anhydride,myclozolin, N-3,5-dichlorophenyl-succinimide,N-3-nitrophenylitaconimide, natamycin,N-ethylmercurio-4-toluenesulfonanilide, nickelbis(dimethyldithiocarbamate), OCH, phenylmercurydimethyldithiocarbamate, phenylmercury nitrate, phosdiphen, prothiocarb,prothiocarb hydrochloride, pyracarbolid, pyridinitril, pyroxychlor,pyroxyfur, quinacetol, quinacetol sulfate, quinazamid, quinconazole,rabenzazole, salicylanilide, SSF-109, sultropen, tecoram, thiadifluor,thicyofen, thiochlorfenphim, thiophanate, thioquinox, tioxymid,triamiphos, triarimol, triazbutil, trichlamide, urbacid, zarilamid, andany combinations thereof.

The compositions of the present disclosure are preferably applied in theform of a formulation comprising a composition of (a) a compound ofFormula I and (b) at least one fungicide selected from the groupconsisting of pyraclostrobin, fluoxastrobin, azoxystrobin,trifloxystrobin, picoxystrobin, kresoxim-methyl, fluxapyroxad,benzovindiflupyr, penthiopyrad, isopyrazam, boscalid, fluopyram,prothioconazole, epoxiconazole, cyproconazole, myclobutanil,metconazole, difenoconazole, propiconazole, fluquinconazole, flutriafol,mancozeb and chlorothalonil, together with a phytologically acceptablecarrier.

Concentrated formulations can be dispersed in water, or another liquid,for application, or formulations can be dust-like or granular, which canthen be applied without further treatment. The formulations are preparedaccording to procedures which are conventional in the agriculturalchemical art, but which are novel and important because of the presencetherein of a synergistic composition.

The formulations that are applied most often are aqueous suspensions oremulsions. Either such water-soluble, water-suspendable, or emulsifiableformulations are solids, usually known as wettable powders, or liquids,usually known as emulsifiable concentrates, aqueous suspensions, orsuspension concentrates. The present disclosure contemplates allvehicles by which the synergistic compositions can be formulated fordelivery and use as a fungicide.

As will be readily appreciated, any material to which these synergisticcompositions can be added may be used, provided they yield the desiredutility without significant interference with the activity of thesesynergistic compositions as antifungal agents.

Wettable powders, which may be compacted to form water-dispersiblegranules, comprise an intimate mixture of the synergistic composition, acarrier and agriculturally acceptable surfactants. The concentration ofthe synergistic composition in the wettable powder is usually from about10% to about 90% by weight, more preferably about 25% to about 75% byweight, based on the total weight of the formulation. In the preparationof wettable powder formulations, the synergistic composition can becompounded with any of the finely divided solids, such as prophyllite,talc, chalk, gypsum, Fuller's earth, bentonite, attapulgite, starch,casein, gluten, montmorillonite clays, diatomaceous earths, purifiedsilicates or the like. In such operations, the finely divided carrier isground or mixed with the synergistic composition in a volatile organicsolvent. Effective surfactants, comprising from about 0.5% to about 10%by weight of the wettable powder, include sulfonated lignins,naphthalenesulfonates, alkylbenzenesulfonates, alkyl sulfates, andnon-ionic surfactants, such as ethylene oxide adducts of alkyl phenols.

Emulsifiable concentrates of the synergistic composition comprise aconvenient concentration, such as from about 10% to about 50% by weight,in a suitable liquid, based on the total weight of the emulsifiableconcentrate formulation. The components of the synergistic compositions,jointly or separately, are dissolved in a carrier, which is either awater-miscible solvent or a mixture of water-immiscible organicsolvents, and emulsifiers. The concentrates may be diluted with waterand oil to form spray mixtures in the form of oil-in-water emulsions.Useful organic solvents include aromatics, especially the high-boilingnaphthalenic and olefinic portions of petroleum such as heavy aromaticnaphtha. Other organic solvents may also be used, such as, for example,terpenic solvents, including rosin derivatives, aliphatic ketones, suchas cyclohexanone, and complex alcohols, such as 2-ethoxyethanol.

Emulsifiers which can be advantageously employed herein can be readilydetermined by those skilled in the art and include various nonionic,anionic, cationic and amphoteric emulsifiers, or a blend of two or moreemulsifiers. Examples of nonionic emulsifiers useful in preparing theemulsifiable concentrates include the polyalkylene glycol ethers andcondensation products of alkyl and aryl phenols, aliphatic alcohols,aliphatic amines or fatty acids with ethylene oxide, propylene oxidessuch as the ethoxylated alkyl phenols and carboxylic esters solubilizedwith the polyol or polyoxyalkylene. Cationic emulsifiers includequaternary ammonium compounds and fatty amine salts. Anionic emulsifiersinclude the oil-soluble salts (e.g., calcium) of alkylaryl sulfonicacids, oil-soluble salts or sulfated polyglycol ethers and appropriatesalts of phosphated polyglycol ether.

Representative organic liquids which can be employed in preparing theemulsifiable concentrates of the present disclosure are the aromaticliquids such as xylene, propyl benzene fractions, or mixed naphthalenefractions, mineral oils, substituted aromatic organic liquids such asdioctyl phthalate, kerosene, dialkyl amides of various fatty acids,particularly the dimethyl amides of fatty glycols and glycol derivativessuch as the n-butyl ether, ethyl ether or methyl ether of diethyleneglycol, and the methyl ether of triethylene glycol. Mixtures of two ormore organic liquids are also often suitably employed in the preparationof the emulsifiable concentrate. The preferred organic liquids arexylene, and propyl benzene fractions, with xylene being most preferred.The surface-active dispersing agents are usually employed in liquidformulations and in the amount of from 0.1 to 20 percent by weight ofthe combined weight of the dispersing agent with the synergisticcompositions. The formulations can also contain other compatibleadditives, for example, plant growth regulators and other biologicallyactive compounds used in agriculture.

Aqueous suspensions comprise suspensions of one or more water-insolublecompounds, dispersed in an aqueous vehicle at a concentration in therange from about 5% to about 70% by weight, based on the total weight ofthe aqueous suspension formulation. Suspensions are prepared by finelygrinding the components of the synergistic combination either togetheror separately, and vigorously mixing the ground material into a vehiclecomprised of water and surfactants chosen from the same types discussedabove. Other ingredients, such as inorganic salts and synthetic ornatural gums, may also be added to increase the density and viscosity ofthe aqueous vehicle. It is often most effective to grind and mix at thesame time by preparing the aqueous mixture and homogenizing it in animplement such as a sand mill, ball mill, or piston-type homogenizer.

The synergistic composition may also be applied as a granularformulation, which is particularly useful for applications to the soil.Granular formulations usually contain from about 0.5% to about 10% byweight of the compounds, based on the total weight of the granularformulation, dispersed in a carrier which consists entirely or in largepart of coarsely divided attapulgite, bentonite, diatomite, clay or asimilar inexpensive substance. Such formulations are usually prepared bydissolving the synergistic composition in a suitable solvent andapplying it to a granular carrier which has been preformed to theappropriate particle size, in the range of from about 0.5 to about 3 mm.Such formulations may also be prepared by making a dough or paste of thecarrier and the synergistic composition, and crushing and drying toobtain the desired granular particle.

Dusts containing the synergistic composition are prepared simply byintimately mixing the synergistic composition in powdered form with asuitable dusty agricultural carrier, such as, for example, kaolin clay,ground volcanic rock, and the like. Dusts can suitably contain fromabout 1% to about 10% by weight of the synergistic composition/carriercombination.

The formulations may contain agriculturally acceptable adjuvantsurfactants to enhance deposition, wetting and penetration of thesynergistic composition onto the target crop and organism. Theseadjuvant surfactants may optionally be employed as a component of theformulation or as a tank mix. The amount of adjuvant surfactant willvary from 0.01 percent to 1.0 percent volume per volume (v/v) based on aspray-volume of water, preferably 0.05 to 0.5 percent. Suitable adjuvantsurfactants include ethoxylated nonyl phenols, ethoxylated synthetic ornatural alcohols, salts of the esters or sulfosuccinic acids,ethoxylated organosilicones, ethoxylated fatty amines and blends ofsurfactants with mineral or vegetable oils.

The formulations may optionally include combinations that can compriseat least 1% by weight of one or more of the synergistic compositionswith another pesticidal compound. Such additional pesticidal compoundsmay be fungicides, insecticides, nematocides, miticides,arthropodicides, bactericides or combinations thereof that arecompatible with the synergistic compositions of the present disclosurein the medium selected for application, and not antagonistic to theactivity of the present compounds. Accordingly, in such embodiments theother pesticidal compound is employed as a supplemental toxicant for thesame or for a different pesticidal use. The pesticidal compound and thesynergistic composition can generally be mixed together in a weightratio of from 1:100 to 100:1.

The present disclosure includes within its scope methods for the controlor prevention of fungal attack. These methods comprise applying to thelocus of the fungus, or to a locus in which the infestation is to beprevented (for example applying to wheat or barley plants), afungicidally effective amount of the synergistic composition. Thesynergistic composition is suitable for treatment of various plants atfungicidal levels, while exhibiting low phytotoxicity. The synergisticcomposition is useful in a protectant or eradicant fashion. Thesynergistic composition is applied by any of a variety of knowntechniques, either as the synergistic composition or as a formulationcomprising the synergistic composition. For example, the synergisticcompositions may be applied to the roots, seeds or foliage of plants forthe control of various fungi, without damaging the commercial value ofthe plants. The synergistic composition is applied in the form of any ofthe generally used formulation types, for example, as solutions, dusts,wettable powders, flowable concentrates, or emulsifiable concentrates.These materials are conveniently applied in various known fashions.

The synergistic composition has been found to have significantfungicidal effect, particularly for agricultural use. The synergisticcomposition is particularly effective for use with agricultural cropsand horticultural plants, or with wood, paint, leather or carpetbacking.

In particular, the synergistic composition is effective in controlling avariety of undesirable fungi that infect useful plant crops. Thesynergistic composition may be used against a variety of Ascomycete andBasidiomycete fungi, including for example the following representativefungi species: wheat brown rust (Puccinia triticina; Synonym Pucciniarecondita f. sp. tritici; Bayer code PUCCRT); stripe rust of wheat(Puccinia striiformis; Bayer code PUCCST); leaf blotch of wheat(Mycosphaerella graminicola; anamorph: Septoria tritici; Bayer codeSEPTTR); glume blotch of wheat (Leptosphaeria nodorum; Bayer codeLEPTNO; anamorph: Stagonospora nodorum); spot blotch of barley(Cochliobolus sativum; Bayer code COCHSA; anamorph: Helminthosporiumsativum); leaf spot of sugar beets (Cercospora beticola; Bayer codeCERCBE); leaf spot of peanut (Mycosphaerella arachidis; Bayer codeMYCOAR; anamorph: Cercospora arachidicola); cucumber anthracnose(Glomerella lagenarium; anamorph: Colletotrichum lagenarium; Bayer codeCOLLLA) and black sigatoka disease of banana (Mycosphaerella fijiensis;BAYER code MYCOFI). It will be understood by those in the art that theefficacy of the synergistic compositions for one or more of theforegoing fungi establishes the general utility of the synergisticcompositions as fungicides.

The synergistic compositions have a broad range of efficacy as afungicide. The exact amount of the synergistic composition to be appliedis dependent not only on the relative amounts of the components, butalso on the particular action desired, the fungal species to becontrolled, and the stage of growth thereof, as well as the part of theplant or other product to be contacted with the synergistic composition.Thus, formulations containing the synergistic composition may not beequally effective at similar concentrations or against the same fungalspecies.

The synergistic compositions are effective in use with plants in adisease-inhibiting and phytologically acceptable amount. The term“disease-inhibiting and phytologically acceptable amount” refers to anamount of the synergistic composition that kills or inhibits the plantdisease for which control is desired, but is not significantly toxic tothe plant. The exact concentration of synergistic composition requiredvaries with the fungal disease to be controlled, the type of formulationemployed, the method of application, the particular plant species,climate conditions, and the like.

The present compositions can be applied to fungi or their locus by theuse of conventional ground sprayers, granule applicators, and by otherconventional means known to those skilled in the art.

The following examples are provided for illustrative purposes and shouldnot be construed as limitations to the disclosure.

EXAMPLES

Evaluation of Curative and Protectant Activity of Fungicide Mixtures Vs.Leaf Blotch of Wheat (Mycosphaerella graminicola; Anamorph: Septoriatritici; Bayer Code: SEPTTR):

Wheat plants (variety Yuma) were grown from seed in a greenhouse inplastic pots with a surface area of 27.5 square centimeters (cm²)containing 50% mineral soil/50% soil-less Metro mix, with 8-12 seedlingsper pot. The plants were employed for testing when the first leaf wasfully emerged, which typically took 7 to 8 days after planting. Testplants were inoculated with an aqueous spore suspension of Septoriatritici either 3 days prior to (3-day curative test) or 1 day afterfungicide treatments (1-day protectant test). After inoculation theplants were kept in 100% relative humidity (one day in a dark dewchamber followed by two days in a lighted mist chamber) to permit sporesto germinate and infect the leaf. The plants were then transferred to agreenhouse for disease to develop.

Treatments consisted of fungicide compounds pyraclostrobin,fluoxastrobin, azoxystrobin, trifloxystrobin, picoxystrobin,kresoxim-methyl, fluxapyroxad, benzovindiflupyr, penthiopyrad,isopyrazam, boscalid, fluopyram, prothioconazole, epoxiconazole,cyproconazole, myclobutanil, metconazole, difenoconazole, propiconazole,fluquinconazole, flutriafol, mancozeb and chlorothalonil, either usingindividually or as two-way mixtures with the compound of Formula I.

Detailed dose-responses of each fungicide in 1-day protectant (1DP) and3-day curative (3DC) SEPTTR whole plant assays were performed usinghigh-volume spray applications, and EC₅₀ values were calculated usingJMP Pro 9.0. With the exception of isopyrazam, fluxapyroxad andpenthiopyrad, compounds were tested as technical grade materialformulated in acetone, and spray solutions contained 10% acetone and 100parts per million (ppm) Triton X-100. Commercially available ECformulations Seguris Flexi and Imtrex were used for isopyrazam andfluxapyroxad respectively, and the SC Fontelis for penthiopyrad. 10% ECand SC formulations of Compound I were also used to determine their EC₅₀values. Compound I was mixed with each fungicide based on EC₅₀ valuesfor protectant and curative activities, respectively. The EC formulationfor Compound I was mixed with isopyrazam and fluxapyroxad, and the SCwith penthiopyrad; the remaining mixtures involved technical materialsfor both Compound I and its mixing partners.

Ten milliliter (mL) fungicide solutions were applied onto 8 pots ofplants using an automated booth sprayer, which utilized two 6218-1/4JAUPM spray nozzles operating at 20 pounds per square inch (psi) set atopposing angles to cover both leaf surfaces. All sprayed plants wereallowed to air dry prior to further handling. Control plants weresprayed in the same manner with the solvent blank.

When disease fully developed on the control plants, infection levelswere assessed on treated plants visually and scored on a scale of 0 to100 percent. Percentage of disease control was then calculated using theratio of disease on treated plants relative to control plants.

Colby's equation was used to determine the fungicidal effects expectedfrom the mixtures. (See Colby, S. R. Calculation of the synergistic andantagonistic response of herbicide combinations. Weeds 1967, 15, 20-22.)

The following equation was used to calculate the expected activity ofmixtures containing two active ingredients, A and B:

Expected=A+B−(A×B/100)

A=observed efficacy of active component A at the same concentration asused in the mixture;

B=observed efficacy of active component B at the same concentration asused in the mixture.

Representative synergistic interactions are presented in Tables 1 and 2.

TABLE 1 Synergistic Interactions of the Compound of Formula I and OtherFungicides in 1-Day Protectant (1 DP) Septoria tritici (SEPTTR) Tests.Rates SEPTTR* Synergism Composition (ppm)* Observed* Expected* Factor*Cmpd. I + Epoxiconazole 1.18 + 0.06 89 70 1.26 Cmpd. I + Cyproconazole1.18 + 0.26 91 81 1.13 Cmpd. I + Metconazole 1.18 + 0.04 86 71 1.21Cmpd. I + Myclobutanil 1.18 + 4.81 95 70 1.35 Cmpd. I + Propiconazole1.18 + 0.04 96 67 1.43 Cmpd. I + Prothioconazole 1.18 + 0.64 90 70 1.29Cmpd. I + Picoxystrobin 1.18 + 3.08 85 75 1.14 Cmpd. I + Trifloxystrobin1.18 + 0.3  84 73 1.15 Cmpd. I + Azoxystrobin 1.18 + 0.64 94 67 1.39Cmpd. I + Fluoxastrobin 1.18 + 0.17 89 74 1.20 Cmpd. I + Boscalid 1.18 +1.56 79 67 1.18 Cmpd. I^(a) + Isopyrazam 8.41 + 10.9 100 91 1.10 Cmpd.I^(a) + Fluxapyroxad 8.41 + 1.92 100 42 2.41 Cmpd. I^(b) + Penthiopyrad2.56 + 4.98 100 59 1.68 Cmpd. I + Benzovindiflupyr 1.18 + 0.15 49 321.50 Cmpd. I + Fluquinconazole  1.18 + 0.007 39 31 1.25 Cmpd. I +Difenoconazole  1.18 + 0.0015 46 33 1.38 Cmpd. I + Pyraclostrobin 1.18 + 0.028 46 40 1.16 Cmpd. I + Fluopyram 1.18 + 4.19 43 34 1.26Cmpd. I + Flutriafol 1.18 + 0.23 30 27 1.10 Cmpd. I + Kresoxim-methyl1.18 + 25  51 35 1.45 Cmpd. I + Chlorothalonil 1.18 + 258  41 31 1.30Cmpd. I + Mancozeb 1.18 + 321  42 31 1.34 *SEPTTR = Leaf Blotch ofWheat; Septoria tritici *DC Observed = Observed disease control at thetest rates *DC Expected = Disease control expected as predicted by theColby equation *ppm = Parts per million *Synergism factor = % DCObserved/% DC Expected *Cmpd I^(a) = An EC formulation of compound I wasused *Cmpd I^(b) = An SC formulation of compound I was used

TABLE 2 Synergistic Interactions of the Compound of Formula I and OtherFungicides in 3-Day Curative (3 DC) Septoria tritici (SEPTTR) Tests.Rates SEPTTR* Synergism Composition (ppm)* Observed* Expected* Factor*Cmpd. I + Epoxiconazole 0.18 + 0.05 99 77 1.29 Cmpd. I + Cyproconazole0.18 + 0.54 98 84 1.17 Cmpd. I + Metconazole 0.18 + 0.08 93 67 1.38Cmpd. I + Myclobutanil 0.18 + 4.86 94 62 1.51 Cmpd. I + Propiconazole0.18 + 0.38 77 52 1.48 Cmpd. I + Prothioconazole 0.18 + 3.89 58 50 1.18Cmpd. I + Picoxystrobin 0.18 + 5.4  68 92 0.73 Cmpd. I + Trifloxystrobin0.18 + 1.74 69 95 0.73 Cmpd. I + Azoxystrobin 0.18 + 0.83 61 79 0.77Cmpd. I + Fluoxastrobin 0.18 + 0.29 51 78 0.65 Cmpd. I + Boscalid 0.18 +2.37 43 93 0.46 Cmpd. I^(a) + Isopyrazam 2.27 + 2.19 74 64 1.15 Cmpd.I^(a) + Fluxapyroxad 2.27 + 0.36 71 53 1.33 Cmpd. I^(b) + Penthiopyrad 0.2 + 0.86 77 61 1.25 Cmpd. I + Benzovindiflupyr 0.18 + 0.54 72 56 1.29Cmpd. I + Fluquinconazole 0.18 + 0.24 27 64 0.42 Cmpd. I +Difenoconazole  0.18 + 0.0015 21 62 0.33 Cmpd. I + Pyraclostrobin 0.18 + 0.009 71 59 1.20 Cmpd. I + Fluopyram 0.18 + 4.96 78 51 1.54Cmpd. I + Flutriafol 0.18 + 3.7  81 64 1.27 Cmpd. I + Kresoxim-methyl0.18 + 45  23 42 0.54 *SEPTTR = Leaf Blotch of Wheat; Septoria tritici*DC Observed = Observed disease control at the test rates *DC Expected =Disease control expected as predicted by the Colby equation *ppm = Partsper million *Synergism factor = % DC Observed/% DC Expected *Cmpd I^(a)= An EC formulation of compound I was used *Cmpd I^(b) = An SCformulation of compound I was used

What is claimed:
 1. A synergistic fungicidal mixture, comprising: afungicidally effective amount of the compound of Formula I:

and at least one additional fungicide in which the at least oneadditional fungicide is a succinate dehydrogenase inhibitor.
 2. Themixture of claim 1 in which the at least one additional fungicide isselected from the group consisting of fluxapyroxad, benzovindiflupyr,penthiopyrad, isopyrazam, boscalid, and fluopyram.
 3. The mixture ofclaim 2 in which the concentration ratio of the Compound of Formula I tofluxapyroxad is between about 4.4:1 and about 6.3:1.
 4. The mixture ofclaim 2 in which the concentration ratio of the Compound of Formula I tobenzovindiflupyr is between about 1:3 and about 7.9:1.
 5. The mixture ofclaim 2 in which the concentration ratio of the Compound of Formula I topenthiopyrad is between about 1:4.3 and about 1:1.9.
 6. The mixture ofclaim 2 in which the concentration ratio of the Compound of Formula I toisopyrazam is between about 1:1.3 and about 1:1.
 7. The mixture of claim2 in which the concentration ratio of the Compound of Formula I toboscalid is between about 1:13.2 and about 1:1.3.
 8. The mixture ofclaim 2 in which the concentration ratio of the Compound of Formula I tofluopyram is between about 1:27.6 and about 1:3.6.
 9. The mixtures ofclaims 1-8, wherein the mixture provides control of a fungal pathogenand the fungal pathogen is one of Leaf Blotch of Wheat (Mycosphaerellagraminicola; anamorph: Septoria tritici), Wheat Brown Rust (Pucciniatriticina), Stripe Rust (Puccinia striiformis f. sp. tritici), Scab ofApple (Venturia inaequalis), Blister Smut of Maize (Ustilago maydis),Powdery Mildew of Grapevine (Uncinula necator), Barley scald(Rhynchosporium secalis), Blast of Rice (Magnaporthe grisea), Rust ofSoybean (Phakopsora pachyrhizi), Glume Blotch of Wheat (Leptosphaerianodorum), Powdery Mildew of Wheat (Blumeria graminis f. sp. tritici),Powdery Mildew of Barley (Blumeria graminis f. sp. hordei), PowderyMildew of Cucurbits (Erysiphe cichoracearum), Anthracnose of Cucurbits(Glomerella lagenarium), Leaf Spot of Beet (Cercospora beticola), EarlyBlight of Tomato (Alternaria solani), and Net Blotch of Barley(Pyrenophora teres).
 10. The mixtures of claims 1-8, wherein the mixtureprovides control of a fungal pathogen and the fungal pathogen is LeafBlotch of Wheat (Mycosphaerella graminicola; anamorph: Septoriatritici).
 11. The mixture of claim 2, wherein the mixture providescontrol of a fungal pathogen and the fungal pathogen is one of LeafBlotch of Wheat (Mycosphaerella graminicola; anamorph: Septoriatritici), Wheat Brown Rust (Puccinia triticina), Stripe Rust (Pucciniastriiformis f. sp. tritici), Scab of Apple (Venturia inaequalis),Blister Smut of Maize (Ustilago maydis), Powdery Mildew of Grapevine(Uncinula necator), Barley scald (Rhynchosporium secalis), Blast of Rice(Magnaporthe grisea), Rust of Soybean (Phakopsora pachyrhizi), GlumeBlotch of Wheat (Leptosphaeria nodorum), Powdery Mildew of Wheat(Blumeria graminis f. sp. tritici), Powdery Mildew of Barley (Blumeriagraminis f. sp. hordei), Powdery Mildew of Cucurbits (Erysiphecichoracearum), Anthracnose of Cucurbits (Glomerella lagenarium), LeafSpot of Beet (Cercospora beticola), Early Blight of Tomato (Alternariasolani), and Net Blotch of Barley (Pyrenophora teres).
 12. The mixtureof claim 2, wherein the mixture provides control of a fungal pathogenand the fungal pathogen is Leaf Blotch of Wheat (Mycosphaerellagraminicola; anamorph: Septoria tritici).
 13. A synergistic, fungicidalcomposition comprising a fungicidally effective amount of the mixturesof claims 1-8 and an agriculturally acceptable adjuvant or carrier. 14.The mixture of claim 1 in which the at least one additional fungicide isfluxapyroxad.
 15. The mixture of claim 1 in which the at least oneadditional fungicide is penthiopyrad.
 16. The mixture of claim 1 inwhich the at least one additional fungicide is benzovindiflupyr.
 17. Themixture of claim 1 in which the at least one additional fungicide isfluopyram.
 18. The mixture of claim 1 in which the at least oneadditional fungicide is isopyrazam.
 19. The mixture of claim 1 in whichthe at least one additional fungicide is boscalid.